Thioglycolic Acid → HCID 53890201, compound

HRID 1655416Notes

Reaction equation

HRID 1655416 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].C[O-].[Na+].[CH:9]12[O:14][CH:10]1[CH2:11][CH2:12][CH2:13]2>CO>[OH:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][C@H:9]1[S:1][CH2:2][C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 10942334Sodium Methoxide

Product 1

HCID 53890201HCID 53890201, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mercaptoacetic acid (22.5g 0.244 mole) was added to a cold (+5° C.) solution of sodium methoxide [prepared from sodium (11.2 g, 0.488 mole)] in methanol (125 ml). After stirring for 20 minutes, cyclopentene oxide (19.5 g, 0.23 mole) was added dropwise over 20 minutes to the cold solution. The ice bath was removed and the reaction was refluxed for 45 minutes. The reaction was cooled to room temperature and made acidic by the addition of 4N hydrochloric acid. Water (100 ml) was added and the mixture was extracted twice with 150 ml of diethyl ether. The combined diethyl ether extracts were washed with water (50 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The structure was confirmed by NMR spectroscopy.

Workup

  1. customThe ice bath was removed
  2. temperaturethe reaction was refluxed for 45 minutes
  3. additionmade acidic by the addition of 4N hydrochloric acid
  4. additionWater (100 ml) was added
  5. extractionthe mixture was extracted twice with 150 ml of diethyl ether
  6. washThe combined diethyl ether extracts were washed with water (50 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to an oil with a rotary evaporator

Sources & evidence

ORD record
ord-d60c5f265cad4b33b3f2b3d3aadaf675
Source dataset
uspto-grants-1993_10
Patent number
US05250567

Reaction notes

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